1H−15N HMBC NMR as a tool for rapid identification of isomeric azaindoles: The case of 5F‐MDMB‐P7AICA. Issue 4 (26th February 2019)

• Record Type: Journal Article
• Authors: Martek, Bruno Aleksander; Mihelač, Mateja; Gazvoda, Martin; Virant, Miha; Urankar, Damijana; Krivec, Marko; Gostič, Tomaž; Nemec, Brigita; Koštrun, Bojana; Janežič, Mojca; Klemenc, Sonja; Košmrlj, Janez
• Is Part Of: Drug testing and analysis. Volume 11:Issue 4(2019)
• Page Start: 617
• Page End: 625
• Publication Date: 2019-02-26
• Subjects: 15N NMR -- 5F‐MDMB‐P7AICA -- azaindole -- new psychoactive substances (NPS) -- synthetic cannabinoid receptor agonists (SCRAs); Drugs -- Analysis -- Periodicals; Drug testing -- Periodicals; Chemistry, Forensic -- Periodicals; 615.1901
• DOI: 10.1002/dta.2573
• Languages: English
• ISSNs: 1942-7603

Abstract

Abstract: The high frequency of the synthetic cannabinoid receptor agonists (SCRAs) emergence renders this group of new psychoactive compounds particularly demanding in terms of detection, identification, and responding. Without the available reference material, one of the specific problems is differentiation and structure elucidation of constitutional isomers. Herein, we report a simple and efficient flow chart diagram applicable for a rapid nuclear magnetic resonance (NMR) identification and differentiation between azaindoles, 4‐, 5‐, 6‐, and 7‐azaindole, which is a common structural motif of synthetic cannabinoids. The flow chart diagram is based on 1 H NMR and 1 H– 15 N NMR spectra, and to prove the concept, it has been tested on 5F‐MDMB‐P7AICA (1 ). Spectral and analytical data including standard 1D and 2D NMR spectra, gas chromatography−mass spectrometry (GC−MS), Fourier transform infrared−attenuated total reflectant (FTIR−ATR), Raman, melting point, and combustion analysis are provided for compound1 . Abstract : A simple and efficient method for rapid identification and differentiation between azaindoles, i.e. 4‐, 5‐, 6‐, and 7‐azaindole, a common structural motif of synthetic cannabinoids, is described. The method is based on 1 H NMR and 1 H–15N NMR spectral analysis. To prove the concept, the method was tested on a newly identified synthetic cannabinoid methyl‐2‐(1‐(5‐fluoropentyl)‐7‐azaindole‐3‐carboxamido)‐3, 3‐dimethylbutanoate, 5F‐MDMB‐P7AICA.